Most memorable first date

[EltonC]

Was out with friends for a concert Friday night. We’re all 65+/- but have known each other since we were in college, spending our time partying and chasing women. We all watched each other meet our wives, we’re all still married to the same women. Our careers took us across the country but in retirement we are all within about 50 miles of each other. As usual, Kevin brought up our single days and wanted to know everyone’s most memorable first date. Mine was definitely Sue.

I met Sue the weekend before classes started freshman year. I’ll spare you the gory details, but she had come to school with her hometown boyfriend, I knew them both from around the dorm and classes. They broke up, I didn’t ask her out because I was friends with her ex, but I did have classes with her and got to know her pretty well. She was cute - tall, thin with a great ass, long wavy black hair, B cup breasts. I was attracted to her but going after a friend’s ex seemed like a bro code violation. And anyway, I was getting plenty of action in the dorm.

Sophomore year comes and we share two classes, MWF 8 and 11 a.m. We got into the habit of going to the library to study during the gap and after a couple of weeks I decided I was going to ask her out. I talked to her ex and he had no problem with it, assured me they were done. So we went out - dinner, a movie, then drinks at a trendy bar with a patio overlooking downtown. She let it be known that her roommate had gone home for the weekend and I could come up later. We could see a storm system off in the distance gradually getting closer, so after a couple of drinks I suggested we head back. About the time we got to my car it started sprinkling, by the time we made it to her dorm it was an absolute deluge. We agreed to wait out the storm and started making out, my hands were definitely roaming around her body.

After a couple of minutes, I started unbuttoning her blouse, revealing a lacy black bra with a front hook that I undid, exposing her little round boobs. I paid her nipples some attention while running a hand under her skirt up and down her thighs, eventually reaching up and pulling her panties down - a lacy black bikini that matched her bra. I pushed her legs apart and leaned down and ate her out, after she came we made out for a bit, she reached down and undid my shorts and pulled my dick out, then leaned over and gave me head. She gagged a little when I came and spilled a bit of my cum but managed to swallow most of it. It was still pouring at this point, so we made out for a while until the storm finally started to let up.

We went up to her room, kicked off our shoes and started making out. I unbuttoned her blouse and pulled her blouse and bra off, then unzipped her skirt and let it fall to the floor. She pulled by shirt off over my head and undid my shorts and pulled them down with my underwear so they fell to the floor. I grabbed her bedspread and spread it out in the middle of the room and we laid down on it and started making out. I pulled her up so she was sitting on my face and pleasured her, after she came she kissed her way down my body and sucked me, swallowing every drop this time.

After a brief rest, we made love face to face lying on our sides and then a second time doggy style. When we finished, she rolled over onto her back and pulled me up so I was straddling her and sucked and jerked me off one last time, finishing me on her boobs. I leaned over and gave her a big kiss and she told me I really needed to go home because she didn’t want her neighbors seeing me come out of her room in the morning. So we got dressed and she escorted me down to the lobby, shared one more big kiss and I left.

We lasted about a month, the sticking point was social activities - I liked floor parties and house parties around campus while she preferred the quite nights in. She didn’t like me going to parties without her, but when she went she did not have a good time. We remained civil with each other, although it was a bit awkward at first. Junior year she got back with her hometown boyfriend and they were engaged by the time senior year came along. By then it was almost like we had never dated. Haven’t had any contact with them since graduation.

[explorer98]

There's a few but the stand-outs are in sharp contrast.

When I was 20, I'd just taken up with a woman 11 years older (much to my delight). We went out (because we couldn't do what we wanted staying in!) and got up to no good in my car for several hours.

It must have been good because the next thing we both knew was sunlight blazing in through the windscreen and Jenny still curled up naked on my lap in the passenger seat!

42 years ago but babe, you were amazing!!

A little later - and far more 'amusing' was a woman I worked with and who subsequently became the mother of my daughter and has shared life and home with me for 37 years now (despite our 'ups, downs and abouts'!!) delicately trying to explain to me at the moment of our first intimacy that what she really wanted was anal sex!!

She's 68 now and still loves it in the ass!!

[Gnome72141]

Had an online date way back before it was cool...to this day nearly 30 years ago, she was still one of the most physically attractive women I have ever met. She was really conservative and very immature (just moved out of her parents house at 25yo and her parents were paying for her apartment and impressive sports car because she had never had a job yet). Anyway, after dinner we went back to her place to watch a movie, which was her idea. I could already tell that I was friend-zoned, but I decided to roll with it.

We get back to her apartment (she had one other roommate), and she showed me her bedroom as though she was still in college and it was her dorm. She laid down on her bed and said it was so comfortable. It was like hanging out with a cousin as a kid; it was really awkward. Then she said she was going to put pjs on. Took off her top and bra (but faced away from me) and put on a very unflattering pj top. Then took off her jeans (I just saw her black underwear from behind; non-descript), and she put on unappealing pj bottoms.

Then, instead of a movie, she showed me her photo album from a trip to France that she just took. In the album, I saw all these photos of her friends topless on the beach. I asked if she went topless, and she was like, "No way! No guy will see my boobs until we are married!" Yet she literally just changed her clothes in front of me and we had just met a few hours ago. I only saw her from behind, but still.

Anyway, she acted like she wanted a kiss as I was leaving, so I kissed her, and it was like kissing a cement wall. It was the worst.

So, definitely the most memorable, even if not for reasons that this thread was started.

[eugene0]

I was working construction by a college town when I ran into a friend from another town. He was in college and was going out to a party and asked if I wanted to join him. We swing by and pick up his girlfriend and roommate, who were already tipsy. We were in a single cab truck with him driving so the friend said no problem and sat on my lap. Wasn’t long and she had wiggled her short skirt up and with me having shorts on it was skin on skin. She leans back and whispered “you like that? You are going to love later” I have known this girl a total of 10 minutes. She continues to grind on me until she says “ I think we should go to the creek instead “ so we drove another excruciating 4 miles to an abandoned sand pit. She jumps out of the vehicle and takes off her panties and says” if you want these come get them “ strips naked and jumps in the water. Of course I followed and we were naked and fucking in the pit. I looked over and my buddy had his girlfriend spread out on the picnic table. This girl says you want to go watch? So we sat at the next table and watched this little blonde with nice boobs get moved from position to position. My girl was brunette and I asked her to lay down and spread her legs and let the blonde eat her. She says “ baby I don’t swing that way and if I won’t do it for my fiancé I’m not doing it for you “. It was a perfect first and last date

[karlhein]

I had just broken up with wife #1, who was sort of a cold fish sexually. I was playing raquetball, and a coed, who was in one of my classes was watching. We talked between points, she seemed happy that i was single, wound up inviting me over for pizza. She was cute, but not spectacular, but had one of those mischevious smiles that hinted that she might be hot.
After pizza and a beer or two, we were talking, then making out, then I was unbuttoning her blouse, then sucking her nipples, then we were naked, then i was sliding my big boy into her silky pussy. So far, pretty nice, but pretty standard But, after i got inside her, she started getting noisy, moaning, doing the oh god, oh god thing, until she siezed up and came very hard.
As we were making out, calming down, she said have you cum yet. i said, no, it takes me a while. She got a big smile, wrapped her legs around my waist, and started building up to another orgasm. Turns out, she came 5 times before I blew my load. I stayed the night, came 8 times myself (I was 24), who knows how many times she came, but it was a lot, all very dramatic and noisy. We dated for a year, never missed a single day of having some sort of sex (oral and anal, at her instigation, during her periods), every position imaginable when fucking. Generally, I'd say she came 10 times for every 1 that I did.
All from getting invited to pizza while playing raquetball. I shouldn't have let her go.

[piecenick]

Best 1st date was a date set up by my mother. She worked with this girl who needed a date for a formal company dinner, mom asked if I would take her, can't say no to mom. I picked up Rachel at her apartment, she had a nice figure, but not the prettiest girl in the world, but seemed nice. Her roommate was pretty hot, her BF was there to pick her up.

Rachel and I went to the dinner/dance, sat with my parents, we made a lot of small talk, she was a baseball fan, so we had something in common. She said I this was the first time she went out with a college guy, I wasn't stuck-up like she expected, I talked with a British accent for a while, which she thought was pretty funny.

When I went to drop her off I walked her to the door, she said it was still early, asked me if I wanted to come in for a beer. We sat down on her sofa with our beers, she thanked me for being such a good sport about taking her to the dinner. Then she said "time for payback", with that she stood up, dropped her dress to her feet, then sat down and started rubbing my erection, unzipped me, pulled my pants off and gave me the best BJ I had while I played with her nipples.

I couldn't even thank my mom, or at least tell her why I was thanking her.